cis-3-Hexen-1-ol

cis-3-Hexen-1-ol, also known as (Z)-3-hexen-1-ol and leaf alcohol, is a colorless oily liquid with an intense grassy-green odor of freshly cut green grass and leaves. It is produced in small amounts by most plants and it acts as an attractant to many predatory insects. cis-3-Hexen-1-ol is a very important aroma compound that is used in fruit and vegetable flavors and in perfumes. The yearly production is about 30 tonnes.

cis-3-Hexen-1-ol
Names
Preferred IUPAC name
(3Z)-Hex-3-en-1-ol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.011.994
EC Number
  • 231-192-8
KEGG
RTECS number
  • MP8400000
UNII
  • InChI=1S/C6H12O/c1-2-3-4-5-6-7/h3-4,7H,2,5-6H2,1H3/b4-3- checkY
    Key: UFLHIIWVXFIJGU-ARJAWSKDSA-N checkY
  • InChI=1/C6H12O/c1-2-3-4-5-6-7/h3-4,7H,2,5-6H2,1H3/b4-3-
    Key: UFLHIIWVXFIJGU-ARJAWSKDBI
  • CC\C=C/CCO
Properties
C6H12O
Molar mass 100.159 g/mol
Appearance colorless liquid
Density 0.846 g/cm3
Melting point −61 °C (−78 °F; 212 K)
Boiling point 156.5 °C (313.7 °F; 429.6 K)
very slightly soluble
Solubility soluble in ethanol, ether
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
0
2
0
Flash point 44 °C (111 °F)
Lethal dose or concentration (LD, LC):
4700 mg/kg (rat, oral)
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

cis-3-Hexen-1-ol is an alcohol and its esters are also important flavor and fragrance raw materials. The related aldehyde cis-3-hexenal (leaf aldehyde) has a similar and even stronger smell but is relatively unstable and isomerizes into the conjugated trans-2-hexenal.

This compound has been recognized as a semiochemical involved in mechanisms and behaviors of attraction in diverse animals such as insects and mammals. However, there is no scientific evidence of its aphrodisiac effects in humans. The popular Mexican alcoholic beverage, mezcal, is found to have enhanced concentrations of this compound when a maguey worm is served in the glass.

Human odor perception

A pair of two single-nucleotide polymorphisms, both in the gene for the OR2J3 odor receptor, strongly reduce sensitivity to this odorant.[1]

References
  1. McRae JF, Mainland JD, Jaeger SR, Adipietro KA, Matsunami H, Newcomb RD (2012). "Genetic Variation in the Odorant Receptor OR2J3 is Associated with the Ability to Detect the "Grassy" Smelling Odor, cis-3-hexen-1-ol". Chemical Senses. 37 (7): 585–593. doi:10.1093/chemse/bjs049. PMC 3408771. PMID 22714804.
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